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Related Concept Videos

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.1K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.1K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.7K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

3.5K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
3.5K
Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

7.8K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
7.8K

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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Breaking Bonds at Tin(II): Reductive or Oxidative Addition?

Maximilian Dietz1, Josef T Boronski2, Amelia M Swarbrook1

  • 1Inorganic Chemistry Laboratory, Department of Chemistry, University of Oxford, South Parks Road, Oxford, OX1 3QR, UK.

Angewandte Chemie (International Ed. in English)
|June 2, 2025
PubMed
Summary

This study explores adding various bonds (H-H, Be-Be, B-B, B-H) to tin(II) compounds. Researchers discovered new B-B, Be-Be, and borazine B-H bond additions, challenging traditional reaction classifications.

Keywords:
BerylliumBorazineBoronMain groupOrganometallicsTin

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The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
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Area of Science:

  • Inorganic chemistry
  • Organometallic chemistry
  • Main group chemistry

Background:

  • Tin(II) compounds are versatile precursors in inorganic synthesis.
  • Oxidative addition is a key reaction mechanism in organometallic chemistry.
  • Understanding bond activation at main group metal centers is crucial for developing new synthetic methodologies.

Purpose of the Study:

  • To investigate the addition of H-H, Be-Be, B-B, and B-H bonds to a tin(II) center.
  • To report novel examples of bond additions involving main group elements.
  • To re-evaluate the mechanistic classification of these addition reactions.

Main Methods:

  • Experimental studies involving synthesis and characterization of new compounds.
  • Theoretical investigations using quantum chemical calculations.
  • Analysis of reaction pathways and electronic structures.

Main Results:

  • First reported additions of B-B and Be-Be bonds to a main group metal center.
  • First reported addition of a borazine B-H bond to any element.
  • Experimental and theoretical evidence for these novel bond activations.
  • Quantum chemical calculations suggest a nuanced description beyond simple oxidative addition.

Conclusions:

  • The study expands the scope of known bond activation reactions at main group metal centers.
  • New synthetic pathways involving main group elements have been established.
  • The findings necessitate a re-evaluation of the mechanistic interpretation of these addition reactions.